Agricultural and horticultural disease controller and a method for controlling the diseases

ABSTRACT

A method for using a compound represented by the general formula:                    
     (wherein R 1  and R 2  are the substituents, respectively, defined in the specification) for agricultural and horticultural disease control, and a composition used in said method.

This is a division of application Ser. No. 08/941,762 filed Sep. 30, 1997, now U.S. Pat. No. 6,166,054, which is a continuation-in-part of PCT/JP96/00781, filed Mar. 26, 1996.

TECHNICAL FIELD

The present invention relates to an agricultural and horticultural disease controller containing as an active ingredient a 1,2,3-thiadiazole derivative represented by the general formula (1), or a salt thereof:

wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} a group represented by the formula:

(wherein R³ and R⁴, which may be the same or different, are hydrogen atoms, (C₁-C₁₂)alkyl groups or halo(C₁-C₁₂)alkyl groups, m is zero or an integer of 1 to 6, and R⁵ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups), {circle around (12)} a group represented by the formula:

(wherein R³, R⁴ and m are as defined above, and R⁶ and R⁷, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups; (C₁-C₁₂)alkylthio(C₁-C₆)alkyl groups; cyano(C₁-C₁₂)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; unsubstituted phenyl(C₁-C₆)alkyl groups; or substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; R⁶ and R⁷ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula:

(wherein R³, R⁴, R⁶ and R⁷, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula:

[wherein R³, R⁴ and n are as defined above, A is

(wherein R⁹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group),

—S—,

—So—,

—SO₂—,

 {wherein R⁹ is as defined above, and R¹⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group, R⁹ and R¹⁰ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or

N—R¹¹

 (wherein R¹¹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group)}, or

—N(R¹⁰)

 (wherein R¹⁰ is as defined above), and R⁸ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group; a (C₁-C₁₂)alkylthio(C₁-C₁₂)alkyl group; a cyano(C₁-C₁₂)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups], and R² is (i) a group represented by the formula:

—X—R¹²

 [wherein X is an oxygen atom or a sulfur atom, and R¹² is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a hydroxy(C₁-C₆)alkyl group, {circle around (9)} a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group, {circle around (10)} a (C₁-C₁₂)alkylthio(C₁-C₁₂)alkyl group, {circle around (11)} a (C₃-C₆)cycloalkyl group, {circle around (12)} a (C₃-C₆)cycloalkyl(C₁-C₁₂)alkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups, (C₂-C₆)alkynyl groups, and (C₁-C₆)alkoxycarbonyl (C₁-C₆)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (16)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (17)} a diphenyl(C₁-C₆)alkyl group, {circle around (18)} a phenoxy(C₁-C₆)alkyl group, {circle around (19)} a group represented by the formula:

—B—N(R¹³)R¹⁴

 {wherein B is a (C₁-C₆)alkylene group which may be substituted by a (C₁-C₆)alkyl group or a phenyl group, and R¹³ and R¹⁴, which may be the same or different, are hydrogen atoms; formyl groups; (C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₆)alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent; R¹³ and R¹⁴ being able to be taken together to represent a (C₄-C₅)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or

N—R¹¹

 (wherein R¹¹ is as defined above)}, {circle around (20)} a group represented by the formula:

—C(R¹⁵)═C(R¹⁶)—R¹⁷

 (wherein R¹⁵ is a hydrogen atom or a (C₁-C₆)alkyl group, R¹⁶ is a hydrogen atom, a halogen atom or a (C₁-C₆)alkyl group, and R¹⁷ is a nitro group, a cyano group, a (C₁-C₆)alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted amino-carbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C₁-C₁₂)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, R¹⁵ and R¹⁷ being able to be taken together to represent a (C₃-C₆)alkylene group which may be substituted by one or more (C₁-C₆)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula:

 (wherein two R¹⁸'s, which may be the same or different, are hydrogen atoms, (C₁-C₆)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)-alkyl group as the substituent, and l is zero or an integer of 1 to 12), {circle around (22)} a 5- or 6-membered heterocyclic (C₁-C₆)alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C₁-C₁₂)alkyl groups having on the ring a halogen atom or (C₁-C₆)alkyl group as the substituent], (ii) a group represented by the formula:

—O—N═C(R¹⁹)R²⁰

 [wherein R¹⁹ and R²⁰, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (3)} nitro groups, {circle around (4)} cyano groups, {circle around (5)} (C₁-C₁₂)alkyl groups, {circle around (5)} halo(C₁-C₁₂)alkyl groups, {circle around (7)} (C₃-C₆)cycloalkyl groups, {circle around (8)} (C₂-C₁₂)alkenyl groups, {circle around (9)} (C₂-C₁₂)alkynyl groups, {circle around (10)} (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl groups, {circle around (11)} (C₁-C₁₂)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered hetero-cyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (16)} groups represented by the formula;

—SR⁵

 (wherein R⁵ is as defined above), or {circle around (17)} groups represented by the formula:

—N(R⁶)R⁷

 (wherein R⁶ and R⁷ are as defined above), R¹⁹ and R²⁰ being able to be taken together to represent {circle around (18)} a (C₃-C₆)cycloalkane ring or {circle around (19)} a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom], (iii) a group represented by the formula:

—N(R²¹)R²²

 [wherein R²¹ and R²², which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} (C₁-C₁₂)alkyl groups, {circle around (3)} unsubstituted halo(C₁-C₁₂)alkyl groups, {circle around (4)} substituted halo(C₁-C₁₂)alkyl groups having a hydroxyl group or a (C₁-C₆)alkoxy group as the substituent, {circle around (5)} (C₂-C₁₂)alkenyl groups, {circle around (6)} (C₂-C₁₂)alkynyl groups, {circle around (7)} (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups, {circle around (8)} (C₁-C₁₂)alkylthio(C₁-C₆)alkyl groups, {circle around (9)} cyano(C₁-C₁₂)alkyl groups, {circle around (10)} substituted cyano(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C₁-C₆)alkyl groups, {circle around (12)} substituted carbamoyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (13)} hydroxy-(C₁-C₆)alkyl groups, {circle around (14)} di(C₁-C₆)alkoxy(C₁-C₆)alkyl groups in which the (C₁-C₆)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl groups, {circle around (16)} substituted (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenyl group, phenyl(C₁-C₆)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 1) halogen atoms, 2) nitro group, 3) cyano group, 4) (C₁-C₆)alkyl groups, 5) halo(C₁-C₆)alkyl groups, 6) (C₁-C₆)alkoxy groups, 7) halo(C₁-C₆)alkoxy groups, 8) (C₁-C₆)alkylthio groups, 9) halo(C₁-C₆)alkylthio groups, 10) (C₂-C₆)alkenyl groups, 11) (C₂-C₆)alkynyl groups, 12) (C₁-C₆)alkylcarbonyl groups, 13) carboxyl group, 14) (C₁-C₁₂)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula:

 (wherein R²³ and R²⁴, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula:

—SO₂—R²⁵

 (wherein R²⁵ is a hydrogen atom, hydroxyl group, a (C₁-C₁₂)alkyl group, a halo(C₁-C₆)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, unsubstituted 1,2,3-thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C₁-C₆)alkyl group or (C₁-C₆)alkoxy group as the substituent), 19) groups represented by the formula:

 (wherein R²⁵ is as defined above), 20) groups represented by the formula:

 (wherein R²⁶ is a (C₁-C₆)alkyl group, a phenyl group or a phenyl(C₁-C₆)alkyl group), 21) groups represented by the formula:

—NH—SO₂—R²⁵

 (wherein R²⁵ is as defined above), 22) groups represented by the formula:

 (wherein R²⁵ is as defined above), and 23) groups represented by the formula:

 (wherein R²⁶ is as defined above), {circle around (19)} unsubstituted phenyl(C₁-C₆)alkyl groups, {circle around (20)} substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula:

—(CH₂)_(p)NHR¹⁸

 (wherein R¹⁸ is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R²¹ and R²² being able to be taken together to represent {circle around (24)} a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group], (iv) a group represented by the formula:

—N(R⁶)NHR²⁷

 [wherein R⁶ is as defined above, and R²⁷ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a (C₂-C₁₂)alkynyl group, {circle around (6)} a (C₁-C₁₂)alkoxy(C₁-C₆)alkyl group, {circle around (7)} a (C₁-C₁₂)alkylthio(C₁-C₆)alkyl group, {circle around (8)} a cyano(C₁-C₁₂)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (12)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (13)} a group represented by the formula:

 (wherein R⁶ is as defined above), {circle around (14)} a group represented by the formula:

 (wherein R⁶ is as defined above), {circle around (15)} a group represented by the formula:

 (wherein R⁶ and R⁷ are as defined above), or {circle around (16)} a group represented by the formula:

—SO₂—R⁶

 (wherein R⁶ is as defined above)], (v) a group represented by the formula:

—NHN(R⁶)R²⁷

 [wherein R⁶ and R²⁷ are as defined above, R⁶ and R²⁷ being able to be taken together to represent

 ═C(R²⁸)R²⁹

 (wherein R²⁸ and R²⁹, which may be the same or different, are hydrogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkyl groups; (C₃-C₆)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R²⁸ and R²⁹ being able to be taken together to represent a (C₃-C₆)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R⁶ and R²⁷ being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom], or (vi) a group represented by the formula:

—N(R⁶)—OR³⁰

 (wherein R⁶ is as defined above, and R³⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group, a halo(C₁-C₁₂)alkyl group, a (C₃-C₆)cycloalkyl group, a (C₁-C₁₂)alkenyl group, a (C₂-C₁₂)alkynyl group, an unsubstituted phenyl(C₁-C₆)alkyl group, or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups).

BACKGROUND ART

Japanese Patent Unexamined Publication No. 54-9272 discloses 1,2,3-thiadiazole-5-carboxylic acid derivatives, a process for production thereof and an agent containing the derivative and having herbicidal and growth-regulating effects.

DISCLOSURE OF THE INVENTION

The present inventors earnestly investigated for developing a novel agricultural and horticultural disease controller and consequently found that 1,2,3-thiadiazole derivatives or salts thereof, which include some of the compounds disclosed in U.S. Pat. No. 4,177,054, are useful for herbicide and growth segulater, whereby the present invention has been accomplished.

BEST MODE FOR CARRYING OUT THE INVENTION

In the definition of the substituents of the 1,2,3-thiadiazole derivative of the general formula (I) used as the active ingredient of the agricultural and horticultural disease controller of the present invention, the halogen atom includes chlorine atom, bromine atom, iodine atom and fluorine atom. The term “(C₁-C₁₂)alkyl group” means a linear or branched alkyl group of 1 to 12 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl or the like. The term “halo(C₁-C₁₂)alkyl group” means a substituted and linear or branched alkyl group of 1 to 12 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term “(C₂-C₆)alkenyl group” means a linear or branched alkenyl group of 2 to 6 carbon atoms having a double bond. The term “halo-(C₂-C₆)alkenyl group” means a substituted and linear or branched alkenyl group of 2 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different. The term “(C₂-C₆)alkynyl group” means a linear or branched alkynyl group of 2 to 6 carbon atoms having a triple bond. The term “halo(C₂-C₆)alkynyl group” means a substituted and linear or branched alkynyl group of 2 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different.

The term “5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom” means any heterocyclic ring derived from furan, thiophene, pyrrole, oxazole, thiazole, isothiazole, pyrazole, imidazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pynolidine, piperidine, morpholine, thiamorpholine, dithiolane, dithian, piperazine, dioxelan, imidazolizine and the like.

Preferable examples of the substituents of the 1,2,3-thiadiazole derivative of the general formula (I) used in the present invention are as follows. There is preferably used a compound in which R¹ is a (C₁-C₁₂)alkyl group, halo(C₁-C₁₂)alkyl group, (C₃-C₆)cycloalkyl group, (C₂-C₁₂)alkenyl group, halo(C₂-C₁₂)alkenyl group, (C₂-C₁₂)alkynyl group, halo(C₂-C₁₂)alkynyl group, unsubstituted phenyl group or substituted phenyl group, and R² is —X—R¹². There is more preferably used a compound in which R¹ is a (C₁-C₆)alkyl group such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl or n-hexyl, and R² is a hydroxyl group, its salt, a thiol group, its salt, an amide group, or an anilide group.

There is most preferably used a compound in which R¹ is a methyl group and R² is a hydroxyl group, its salt, a thiol group, its salt, an amide group, or an anilide group.

As the salt of the 1,2,3-thiadiazole derivative of the general formula (I), there can be exemplified salts with alkali metals such as sodium, potassium, etc.; salts with alkaline earth metals such as calcium, magnesium, etc.; unsubstituted ammonium salt; substituted ammonium salts having one or more substituents which may be the same or different and are selected from the group consisting of (C₁-C₁₂)alkyl groups, unsubstituted phenyl group, substituted phenyl groups, unsubstituted benzyl group and substituted benzyl groups; and guanidium salt.

The 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof used as the active ingredient of the agricultural and horticultural disease controller of the present invention can be produced, for example, by any of the processes exemplified below:

wherein R¹ is as defined above, R¹ is a (C₁-C₆)alkyl group, R″ is an amino group or a (C₁-C₆)alkyl group, and Hal is a halogen atom.

A compound of the general formula (XII) is reacted with a compound of the general formula (XI) to obtain a compound of the general formula (X). The compound (X) is cyclized after or without isolation to obtain a 1,2,3-thiadiazole derivative of the general formula (I-1). The derivative (I-1) is hydrolyzed after or without isolation to obtain a compound of the general formula (IX). The compound (IX) is halogenated after or without isolation, whereby the acid halide of the general formula (VIII) can be produced.

The compound of the general formula (XII) can be produced by the process described in J. Org. Chem., 43, 2087 (1978), Formation of C—C bonds, Vol. 3, p. 259, 1979 (Georg Thime Publishers, Stuttgart), etc.

From the acid halide of the general formula (VIII) produced by the above process, the 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof used as the active ingredient of the agricultural and horticultural disease controller of the present invention can be produced, for example, by any of the processes illustrated below.

Production Process 1

wherein R¹, R¹², R²¹, R²² and Hal are as defined above.

The acid halide of the general formula (VIII) is reacted with an alcohol of the general formula (III) to obtain a 1,2,3-thiadiazole derivative of the general formula (I-2). The compound (I-2) is reacted with an amine of the general formula (II) after or without isolation of the compound (I-2), whereby a 1,2,3-thiadiazole derivative of the general formula (1I-3) can be produced.

The 1,2,3-thiadiazole derivative of the general formula (I-3) can be produced also by reacting the acid halide of the general formula (VIII) with an amine of the general formula (II).

Production Process 2

wherein R¹⁹, R²⁰ and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-4) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (IV).

Production Process 3

wherein R⁶, R²⁷ and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-5) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (V). Similarly, a 1,2,3-thiadiazole derivative of the general formula (I-6) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (VI).

Production Process 4

wherein R⁶, R³⁰ and Hal are as defined above.

A 1,2,3-thiadiazole derivative of the general formula (I-7) can be produced by reacting the acid halide of the general formula (VIII) with a compound of the general formula (VII).

Typical compounds as the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof are listed in Table 1 but they are not intended in any way to limit the scope of the present invention.

The abbreviations in the R¹ column and R² column in Table 1 stand for the following compounds:

TABLE 1 Ph:

naph:

Q₁:

Q₂:

Q₃:

Q₄:

Q₅:

Q₆:

Q₇:

Q₈:

Q₉:

Q₁₀:

Q₁₁:

Q₁₂:

Q₁₃:

Q₁₄:

Q₁₅:

Q₁₆:

Q₁₇:

Q₁₈:

Q₁₉:

Q₂₀:

Q₂₁:

Q₂₂:

General formula (I) (I)

No R¹ R² Physical property 1 H OH m.p. 107.1° C. 2 H OC₂H₅ nD 1.5060 (20.1° C.) 3 H NH₂ m.p. 160.8° C. 4 H NH—Ph m.p. 132.0° C. 5 H NH—CH(Q₅)—CN m.p. 163.9° C. 6 H NHOCH₃ m.p. 113.1° C. 7 CH₃ OH m.p. 188-189.5° C. 8 CH₃ O—Na m.p. 230° C. (decomp.) 9 CH₃ O—K m.p. 243° C. (decomp.) 10 CH₃ O—Li m.p. 280° C. (decomp.) 11 CH₃ O—Ag m.p. 190° C. (decomp.) 12 CH₃ O—½Ca m.p. 250° C. (decomp.) 13 CH₃ O—NH₄ m.p. 130° C. (decomp.) 14 CH₃ O—NH₂C(NH₂)═NH₂ m.p. 146° C. 15 CH₃ OCH₃ nD 1.5165 (23.2° C.) 16 CH₃ OC₂H₅ nD 1.5075 (14.0° C.) 17 CH₃ OC₃H₇-n nD 1.4000 (12.5° C.) 18 CH₃ OC₃H₇-i nD 1.4400 (14.3° C.) 19 CH₃ OC₄H₉-s nD 1.4165 (24.2° C.) 20 CH₃ OC₄H₉-t nD 1.4245 (16.9° C.) 21 CH₃ OCH(CH₂CH₃)₂ nD 1.3211 (24.5° C.) 22 CH₃ OC₈H₁₇-n nD 1.4900 (12.9° C.) 23 CH₃ OC₁₁H₂₃-n nD 1.4946 (18.4° C.) 24 CH₃ OC₁₅H₃₁-n NMR 25 CH₃ OCH₂CH₂Br + OCH₂CH₂I = 2:1 nD 1.5615 (20.7° C.) 26 CH₃ OCH₂CH═CH₂ nD 1.5153 (15.0° C.) 27 CH₃ O(CH₂)₈CH═CHCH₂CH═(CH₂)₄CH₃ nD 1.502 (26.3° C.) cis cis 28 CH₃ O—CH₂C≡CH nD 1.3405 (13.8° C.) 29 CH₃ O-cyclo-C₆H₁₁ nD 1.5248 (25.2° C.) 30 CH₃ O—CH₂-cyclo-C₃H₅ nD 1.5241 (26.5° C.) 31 CH₃ O—CH₂COOC₂H₅ nD 1.5074 (25.5° C.) 32 CH₃ O—CH₂COCH₃ m.p. 55.7-56.8° C. 33 CH₃ O—Ph nD 1.5845 (20.6° C.) 34 CH₃ O-(4-Cl—Ph) m.p. 77-80° C. 35 CH₃ O-(2-CH₃—Ph) m.p. 62-64° C. 36 CH₃ O-(3-CH₃—Ph) m.p. 51-53° C. 37 CH₃ O-(4-CH₃—Ph) m.p. 31° C. 38 CH₃ O-(4-OCH₃—Ph) m.p. 73° C. 39 CH₃ O-(4-OCH(CH₃)COOC₂H₅—Ph) nD 1.5433 (26.5° C.) 40 CH₃ O—CH₂—Ph nD 1.5735 (13.1° C.) 41 CH₃ O—CH₂-(4-Cl—Ph) m.p. 85° C. 42 CH₃ O—CH₂-(4-NO₂—Ph) m.p. 100° C. 43 CH₃ O—CH₂-(4-CH₃—Ph) m.p. 52° C. 44 CH₃ O—CH₂(4-t-C₄H₉—Ph) nD 1.5558 (26.3° C.) 45 CH₃ O—CH₂(3-O—Ph—Ph) nD 1.6029 (26.4° C.) 46 CH₃ O—CH₂(2,4-Cl₂—Ph) m.p. 74° C. 47 CH₃ O—CH₂(2,6-Cl₂—Ph) m.p. 97° C. 48 CH₃ O—CH₂(3,5-Cl₂—Ph) m.p. 81° C. 49 CH₃ O—CH₂(2-OCH₃—Ph) m.p. 60° C. 50 CH₃ O—CH(Ph)₂ nD 1.6030 (26.4° C.) 51 CH₃ O—CH₂-(4-OCH₃—Ph) nD 1.5774 (26.2° C.) 52 CH₃ O—CH₂—(F₅—Ph) m.p. 61° C. 53 CH₃ O—CH₂CH₂O—Ph m.p. 78° C. 54 CH₃ O—CH(CH₃)—Ph nD 1.5631 (25.0° C.) 55 CH₃ O—CH₂CH₂Si(CH₃)₃ nD 1.501 (20.2° C.) 56 CH₃ O—CH₂—Q₁ nD 1.5730 (28.0° C.) 57 CH₃ O—CH₂-(4-CH₃—Q₈) nD 1.5842 (25.0° C.) 58 CH₃ O—CH₂CH₂O—Q₁₄ m.p. 137° C. 59 CH₃ O—CH₂CH₂—Q₁₅ m.p. 102° C. 60 CH₃ O—CH₂CH₂O—Q₁₀ nD 1.5280 (28.0° C.) 61 CH₃ O—CH₂—Q₇ m.p. 68-74° C. 62 CH₃ O—Q₁₇ nD 1.5678 (28.8° C.) 63 CH₃ O-5,5-(CH₃)₂—Q₁₇) nD 1.5498 (28.7° C.) 64 CH₃ O—CH₂CH₂O—CO-(4-CH₃—Q₈) NMR 65 CH₃ O—N═C₆H₁₀-cyclo nD 1.461 (13.5° C.) 66 CH₃ O—N═C(CH₃)₂ nD 1.5422 (19.8° C.) 67 CH₃ O—N═CH—Ph m.p. 113.5° C. 68 CH₃ O—N═C(CH₃)—Ph m.p. 99.9° C. 69 CH₃ O—Q₁₆ m.p. >185° C. (sublimation) 70 CH₃ O—N═Q₁₂ m.p. 114.5° C. 71 CH₃ O—N═Q₁₃ m.p. 100.1° C. 72 CH₃ SCH₃ m.p. 40.1° C. 73 CH₃ SC₂H₅ nD 1.5229 (20.8° C.) 74 CH₃ SC₃H₇-n nD 1.4499 (20.9° C.) 75 CH₃ SC₃H₇-i nD 1.5620 (21.8° C.) 76 CH₃ SC₄H₉-i nD 1.4546 (21.6° C.) 77 CH₃ SC₄H₉-t nD 1.5743 (21.0° C.) 78 CH₃ SC₈H₁₇-n nD 1.5361 (25.4° C.) 79 CH₃ SC₁₂H₂₅-n nD 1.5261 (18.6° C.) 80 CH₃ S-cyclo-C₆H₁₁ nD 1.5743 (20.8° C.) 81 CH₃ S-(4-CH₃—Ph) nD 1.6261 (21.2° C.) 82 CH₃ S—CH₂—Ph nD 1.6239 (21.1° C.) 83 CH₃ S—CH₂-(4-Cl—Ph) m.p. 74.5° C. 84 CH₃ NH₂ m.p. 115° C. 85 CH₃ NHCH₃ m.p. 45° C. 86 CH₃ N(CH₃)₂ nD 1.5555 (13.2° C.) 87 CH₃ NHC₂H₅ m.p. 44° C. 88 CH₃ N(C₂H₅)₂ nD 1.5365 (13.7° C.) 89 CH₃ NHC₃H₇-i m.p. 65° C. 90 CH₃ NHC₄H₉-n 91 CH₃ NHC₆H₁₁-cyclo m.p. 98° C. 92 CH₃ NHCH₂CH₂OCH₃ nD 1.5359 (26.0° C.) 93 CH₃ NHCH₂CH₂CH₂OCH₃ nD 1.5273 (26.0° C.) 94 CH₃ NHCH₂CH(OCH₃)₂ nD 1.5240 (26.1° C.) 95 CH₃ N(CH₂CH═CH₂)₂ nD 1.5535 (27.5° C.) 96 CH₃ NHC(CH₃)₂—C≡CH NMR 97 CH₃ NHCH(CH₃)CH₂OH NMR 98 CH₃ NHCH₂CN m.p. 76-78° C. 99 CH₃ NHCH₂CH₂CN m.p. 86-87° C. 100 CH₃ N(CH₂CH₂CN)₂ m.p. 110-115° C. 101 CH₃ NHC(CH₃)(i-C₃H₇)—CN nD 1.5235 (25.9° C.) 102 CH₃ NHCH(C₃H₇-i)COOCH₃ NMR 103 CH₃ NHCH(CH₃)CH₂COOC₂H₅ nD 1.5250 (20.4° C.) 104 CH₃ NHPh m.p. 110° C. 105 CH₃ NH(2-Cl—Ph) m.p. 101° C. 106 CH₃ NH(3-Cl—Ph) m.p. 136-142° C. 107 CH₃ NH(4-Cl—Ph) m.p. 114° C. 108 CH₃ NH(2-F—Ph) m.p. 120° C. 109 CH₃ NH(3-F—Ph) m.p. 127° C. 110 CH₃ NH(4-F—Ph) m.p. 103° C. 111 CH₃ NH(2-CH₃—Ph) m.p. 115° C. 112 CH₃ NH(3-CH₃—Ph) m.p. 111° C. 113 CH₃ NH(4-CH₃—Ph) m.p. 109° C. 114 CH₃ NH(3-i-C₃H₇—Ph) NMR 115 CH₃ NH(2-OCH₃—Ph) m.p. 112° C. 116 CH₃ NH(3-OCH₃—Ph) m.p. 107-110° C. 117 CH₃ NH(4-OCH₃—Ph) m.p. 117° C. 118 CH₃ NH(3-O-i-C₃H₇—Ph) NMR 119 CH₃ NH(4-NO₂—Ph) m.p. 175° C. 120 CH₃ NH(3-CN—Ph) m.p. 161° C. 121 CH₃ NH(4-CN—Ph) m.p. 172° C. 122 CH₃ NH(4-CO₂H—Ph) m.p. 257° C. (decomp.) 123 CH₃ NH(4-CO₂CH₃—Ph) m.p. 133° C. 124 CH₃ NH(4-CO₂C₂H₅—Ph) m.p. 118° C. 125 CH₃ NH(3-COCH₃—Ph) m.p. 154° C. 126 CH₃ NH(4-COCH₃—Ph) m.p. 128° C. 127 CH₃ NH(2-Ph—Ph) m.p. 85.5° C. 128 CH₃ NH(2,4-Cl₂—Ph) m.p. 118-119° C. 129 CH₃ NH(2,5-Cl₂—Ph) m.p. 151-155° C. 130 CH₃ NH(3,4-Cl₂—Ph) m.p. 138-139° C. 131 CH₃ NH(3,5-Cl₂—Ph) m.p. 197-199° C. 132 CH₃ NH(2,4-(CH₃)₂—Ph) m.p. 98.3-98.9° C. 133 CH₃ NH(2,6-(CH₃)₂—Ph) m.p. 95-99° C. 134 CH₃ NH(3,5-(CF₃)₂—Ph) m.p. 170° C. 135 CH₃ NH(3-OCH₂O-4-Ph) m.p. 138° C. 136 CH₃ NH(2,4,6-(CH₃)₃—Ph) m.p. 115-117° C. 137 CH₃ NH(2,6-Br₂-4-OCF₃—Ph) m.p. 151.7° C. 138 CH₃ NH(F₅—Ph) m.p. 124° C. 139 CH₃ NH—CH₂—Ph m.p. 53° C. 140 CH₃ N(CH₃)—Ph paste NMR 141 CH₃ NHC(CH₃)₂—Ph m.p. 139° C. 142 CH₃ NHCH₂-(4-Cl—Ph) m.p. 102-105° C. 143 CH₃ NHCH(CH₃)(4-Cl—Ph) m.p. 108° C. 144 CH₃ NHCH(CH₂—Ph)COOCH₃ NMR 145 CH₃ NH-naph m.p. 151° C. 146 CH₃ NH—Q₂ m.p. 130° C. 147 CH₃ Q₁₀ m.p. 92° C. 148 CH₃ 2,6-(CH₃)₂—Q₁₀ m.p. 96-100° C. (cis) 149 CH₃ NHCH₂—Q₃ nD 1.5731 (26.1° C.) 150 CH₃ NHCH(OC₂H₅)—CN paste NMR 151 CH₃ NHCH(OCH₂C≡CH)—CN NMR 152 CH₃ NHCH(Q₅)—CN m.p. 157.3° C. 153 CH₃ NHCH(3,5-(CH₃)₂—Q₅)—CN m.p. 155.6° C. 154 CH₃ NHCH(SCH(CH₃)—C₂H₅)—CN paste NMR 155 CH₃ NHCH(S—Ph)—CN m.p. 116.5° C. 156 CH₃ NHSO₂—Ph m.p. 170-176° C. 157 CH₃ N═C(NH₂)₂ m.p. 245° C. 158 CH₃ NHNH₂ m.p. 143.8° C. 159 CH₃ N(CH₃)NH₂ + NHNHCH₃ = 4:1 m.p. 96.7-104.0° C. 160 CH₃ NHN(CH₃)₂ m.p. 149-154° C. 161 CH₃ NHNHCO—Ph m.p. 183.4° C. 162 CH₃ NH—Q₁₀ m.p. 191.0° C. 163 CH₃ NHN═C(CH₃)₂ m.p. 198° C. 164 CH₃ NHN═C(CH₃)C₂H₅ m.p. 152-153° C. 165 CH₃ NHN═CH—Ph m.p. 238° C. 166 CH₃ NHN═C(cyclo-C₃H₅)Ph m.p. 156° C. (Mixture of E- and Z-forms) 167 CH₃ NHN═C(CH₃)Ph m.p. 260-270° C. 168 CH₃ NHN═C(CH₃)(2-CH₃—Ph) m.p. 146.6° C. (upper spot in TLC) 169 CH₃ NHN═C(CH₃)(2-CH₃—Ph) m.p. 153.0° C. Lower spot in TLC 170 CH₃ NHN═C(CH₃)Q₃ m.p. 286-288° C. 171 CH₃ NHN═C(CH₃)Q₂ m.p. 215-216° C. 172 CH₃ NHN═Q₁₂ m.p. 239.7° C. 173 CH₃ NHOCH₃ m.p. 70° C. 174 CH₃ NHOCH₂—Ph m.p. 73° C. 175 C₂H₅ OH m.p. 137.1-138.4° C. 176 C₂H₅ ONa m.p. 250° C. (decomp.) 177 C₂H₅ O—PhCH₂N(CH₃)₃ m.p. 115-117° C. 178 C₂H₅ O—NH₃C₄H₉-t m.p. 105-107° C. 179 C₂H₅ O-½pyridinium m.p. 62-63° C. 180 C₂H₅ OCH₃ nD 1.5093 (24.1° C.) 181 C₂H₅ OCH₂—Ph nD 1.5539 (23.7° C.) 182 C₂H₅ NH₂ m.p. 139.0° C. 183 C₂H₅ NH—Ph m.p. 81.9° C. 184 n-C₃H₇ OC₂H₅ nD 1.4958 (21.0° C.) 185 i-C₃H₇ OH m.p. 136.6° C. 186 i-C₃H₇ O—Na NMR 187 i-C₃H₇ O—NH₄ m.p. 169.9° C. 188 i-C₃H₇ OC₂H₅ nD 1.4934 (20.9° C.) 189 i-C₃H₇ OC₈H₁₇-n nD 1.4845 (21.8° C.) 190 i-C₃H₇ OCH₂—Ph nD 1.5505 (23.8° C.) 191 i-C₃H₇ NH₂ m.p. 137.3° C. 192 i-C₃H₇ NH—Ph m.p. 112.3° C. 193 i-C₃H₇ NH—CH₂—CN paste NMR 194 i-C₃H₇ NH—CH(Q₅)—CN m.p. 107.4° C. 195 n-C₄H₉ OH m.p. 92.3° C. 196 n-C₄H₉ O—Na m.p. 188.5° C. 197 n-C₄H₉ OCH₃ nD 1.4993 (22.3° C.) 198 t-C₄H₉ OH m.p. 111.1° C. 199 t-C₄H₉ OCH₃ nD 1.5082 (13.0° C.) 200 n-C₅H₁₁ OH m.p. 86.2° C. 201 n-C₅H₁₁ OCH₃ nD 1.4969 (22.5° C.) 202 CH₂Cl OH m.p. 120.9° C. 203 CH₂Cl O—Na m.p. 280° C. (decomp.) 204 CH₂Cl OCH₃ nD 1.5315 (19.2° C.) 205 CH₂Br OH m.p. 117.4° C. 206 CH₂Br OCH₃ nD 1.5743 (13.1° C.) 207 CF₃ OH nD 1.4590 (23.7° C.) 208 CF₃ OCH₃ nD 1.4513 (23.6° C.) 209 CF₃ OC₂H₅ nD 1.4451 (23.6° C.) 210 CF₃ NH₂ m.p. 143.7° C. 211 CF₃ NH—Ph m.p. 142.7° C. 212 CF₃ NH(3-i-C₃H₇—Ph) m.p. 81.3° C. 213 CF₃ NH(3-i-C₃H₇O—Ph) paste NMR 214 CF₃ NH-(3,5-(CF₃)₂—Ph) m.p. 156.2° C. 215 CF₃ NH—CH(Q₅)—CN m.p. 118.9° C. 216 CF₃ NHOCH₃ m.p. 101.9° C. 217 CHBrCH₃ OH m.p. 114.8° C. 218 CHBrCH₃ OCH₃ nD 1.5545 (22.7° C.) 219 CH₂CH₂CH₂Cl OCH₃ nD 1.5271 (24.0° C.) 220 cyclo-C₃H₅ OH m.p. 157.1° C. 221 cyclo-C₃H₅ OCH₃ m.p. 47.4° C. 222 cyclo-C₃H₅ OC₂H₅ nD 1.5304 (22.1° C.) 223 cyclo-C₃H₅ OCH₂—Ph nD 1.5815 (22.1° C.) 224 cyclo-C₃H₅ ON═Q₁₂ m.p. 160.6° C. 225 cyclo-C₃H₅ NH₂ m.p. 162.7° C. 226 cyclo-C₃H₅ NH—Ph m.p. 138.8° C. 227 cyclo-C₃H₅ NH-(3-i-C₃H₇—Ph) paste NMR 228 cyclo-C₃H₅ NH(3-i-C₃H₇O—Ph) paste NMR 229 CH₂OCH₃ OH m.p. 104.8° C. 230 CH₂OCH₃ OCH₃ m.p. 40.4° C. 231 CH₂O—COCH₃ OCH₃ nD 1.5122 (19.1° C.) 232 CH₂S—Ph OH m.p. 133.6° C. 233 CH₂S—Ph OCH₃ nD 1.6210 (19.5° C.) 234 CH₂S-(4-Cl—Ph) OH m.p. 143.8° C. 235 CH₂S-(4-Cl—Ph) OCH₃ nD 1.6268 (19.6° C.) 236 COOH NHC(CH₃)(i-C₃H₇)—CN nD 1.4832 (25.1° C.) 237 COOC₂H₅ OH m.p. 68.9° C. 238 COOC₂H₅ OC₂H₅ nD 1.5008 (21.4° C.) 239 COOC₂H₅ OC₄H₉-n 240 COOC₂H₅ NH—Ph m.p. 125.4° C. 241 COOC₄H₉-n O—C₄H₉-n nD 1.4928 (24.2° C.) 242 COOC₄H₉-n NHCH₂—Ph paste NMR 243 CONHCH₃ NHCH₃ m.p. 195-196° C. 244 CONHC₃H₇-i NHC₃H₇-I m.p. 92-96° C. 245 CONHCH₂CH₂OCH₃ NHCH₂CH₂OCH₃ m.p. 90-92° C. 246 CONHCH₂Ph OC₄H₉-n paste NMR 247 CONHCH₂Ph NHCH₂Ph m.p. 113.8-116.3° C. 248 CON(CH₃)CH₂Ph OC₂H₅ 249 CH₂COOH OH m.p. 159-160° C. (decomp.) 250 CH₂COOCH₃ OCH₃ nD 1.5165 (21.4° C.) 251 CH₂COOCH₃ OC₄H₉-n nD 1.4956 (23.9° C.) 252 CH₂CONHC₃H₇-i NHC₃H₇-i m.p. 146-156° C. 253 CH₂CONHC₅H₁₁-i NHC₅H₁₁-i m.p. 84-86° C. 254 CH₂OH OH m.p. 147.1° C. 255 CH₂OH OCH₃ nD 1.5390 (21.4° C.) 256 CH₂O—CH═C(CN)(4-CH₃—Ph) OC₂H₅ m.p. 69-76° C. 257 CH₂N(CH₃)₂ OCH₃ m.p. 100.1° C. 258 CH₂N(CH₃)—Ph OC₂H₅ nD 1.5761 (24.2° C.) 259 CH₂NHCO-(2-COOH—Ph) OH m.p. 157.5° C. 260 CH₂—Q₁₀ OCH₃ nD 1.5335 (21.6° C.) 261 CH₂-(2,6-(CH₃)₂—Q₁₀) O—Na m.p. 73.7° C. 262 CH₂-(2,6-(CH₃)₂—Q₁₀) OCH₃ nD 1.5169 (21.6° C.) 263 CH₂—Q₁₆ OCH₃ m.p. 155.1° C. 264 CH₂—Q₆ OCH₃ paste NMR 265 CH₂—Q₇ OCH₃ paste NMR 266 Ph OH m.p. 148.5° C. 267 Ph O—Na NMR 268 Ph OC₂H₅ nD 1.5888 (20.8° C.) 269 Ph NH₂ m.p. 185.9° C. 270 Ph NH—CH₂—CN m.p. 147.1° C. 271 Ph NH—CH(Q₅)—CN m.p. 146.3° C. 272 2-F—Ph OH m.p. 138.8° C. 273 2-F—Ph O—Na NMR 274 2-F—Ph OCH₃ nD 1.5611 (22.6° C.) 275 2-F-4-Cl-5-OCH₂COOC₂H₅—Ph OC₂H₅ nD 1.5572 (21.5° C.) 276 CH₂O—Ph OH m.p. 153.9° C. 277 CH₂O—Ph OCH₃ nD 1.5772 (21.5° C.) 278 CH₂O(4-Cl—Ph) OH m.p. 148.2° C. 279 CH₂O(4-Cl—Ph) OCH₃ m.p. 72° C. 280 CH₂O(2-CH₃—Ph) OH m.p. 139.1-140.8° C. 281 CH₂O(2-CH₃—Ph) OC₂H₅ nD 1.5579 (20.1° C.) 282 CH₂ON═C(CH₃)(4-Cl—Ph) OC₂H₅ paste NMR 283 CH₂SO₂Ph OH m.p. 161-162° C. 284 CH₂SO₂Ph OC₂H₅ m.p. 75.6-77.8° C. 285 CH₂SO₂Ph NHCH(CH₃)—Ph m.p. 127-131° C. 286 CH₂S—Q₁₁ OCH₃ nD 1.6145 (24.2° C.) 287 CH₃ NHN═C(CH₃)Q₄ m.p. >280° C. 288 CH₃ NHCH(OC₂H₅)COOC₂H₅ m.p. 68.8° C. 289 CH₃ NHCH(OC₃H₇-i)COOC₂H₅ m.p. 52.1° C. 290 CH₃ NHCH(Q₅)COOC₂H₅ m.p. 107.3° C. 291 CH₃ NHCH(OC₂H₅)CONH₂ m.p. 136.9° C. 292 CH₃ NHCH(CN)OCH₂COOC₂H₅ nD 1.5217 (21.7° C.) 293 CH₃ NHCH(CN)SCH₂COOC₂H₅ nD 1.5525 (21.5° C.) 294 CH₃ NHCH₂COOC₂H₅ nD 1.5248 (21.5° C.) 295 CH₃ NHCH(CCl₃)OH m.p. 150° C. 296 CH₃ NHCH(CCl₃)OC₄H₉-n paste NMR 297 H O—Na 298 H O—C₃H₇-i 299 H O—C₆H₁₃-n 300 H O—C₁₂H₂₅-n 301 H O—Ph 302 H O-(4-Cl—Ph) 303 H O-(4-CH₃—Ph) 304 H O—CH₂—Ph 305 H O—CH₂-(4-Cl—Ph) 306 CH₃ O—C₄H₉-i 307 CH₃ O—C₆H₁₃-n 308 CH₃ O-(2-Cl—Ph) 309 CH₃ O-(3-Cl—Ph) 310 CH₃ O-(2-OCH₃—Ph) 311 CH₃ O-(3-OCH₃—Ph) 312 CH₃ O-(2,4-(Cl)₂—Ph) 313 CH₃ O-(3,4-(Cl)₂—Ph) 314 CH₃ O-(3,5-(Cl)₂—Ph) 315 CH₃ O—CH₂-(2-Cl—Ph) 316 CH₃ O—CH₂-(3-Cl—Ph) 317 CH₃ O—CH₂-(2-CH₃—Ph) 318 CH₃ O—CH₂-(3-CH₃—Ph) 319 CH₃ O—CH₂-(3-OCH₃—Ph) 320 CH₃ O—C(CH₃)₂—Ph) 321 CH₃ O—(CH₂)₃O—CO(4-CH₃—Q₈) 322 CH₃ O—(CH₂)₆O—CO(4-CH₃—Q₈) 323 CH₃ O—(CH₂)₁₂O—CO(4-CH₃—Q₈) 324 CH₃ O—N═C(Cl)—Ph 325 CH₃ O—N═C(CN)—Ph 326 CH₃ O—N═C(CH₃)—C₆H₁₁-cyclo 327 CH₃ O—N═C(CH₃)—CH₂OCH₃ 328 CH₃ O—N═C(CH₃)—COOCH₃ 329 CH₃ O—N═C(COOC₂H₅)₂ 330 CH₃ O—N═C(SCH₃)—Ph 331 CH₃ O—N═C(S—Ph)—Ph 332 CH₃ O—N═C(Ph)—N(CH₃)₂ 333 CH₃ S—Ph 334 CH₃ S-(4-Cl—Ph) 335 CH₃ S-(4-OCH₃—Ph) 336 CH₃ S—CH₂-(4-CH₃—Ph) 337 CH₃ S—CH₂-(4-OCH₃—Ph) 338 CH₃ S—CH₂COOC₂H₅ 339 CH₃ S—Q₂ 340 CH₃ NH(3-C₂H₅—Ph) m.p. 87.4-88.5° C. 341 CH₃ NH(4-C₂H₅—Ph) m.p. 95.1-96.2° C. 342 CH₃ NH(2-COOC₂H₅—Ph) m.p. 63° C. 343 CH₃ NH(3-COOC₂H₅—Ph) paste 344 CH₃ NH(4-COOC₃H₇-i-Ph) m.p. 125.2-127.5° C. 345 CH₃ NH(2-CONH₂—Ph) m.p. 222-223° C. 346 CH₃ NH(3-CONH₂—Ph) m.p. 232° C. 347 CH₃ NH(4-CONH₂—Ph) m.p. 244.8-248.2° C. 348 CH₃ NH(2-CONHCH₃—Ph) m.p. 162° C. 349 CH₃ NH(3-CONHCH₃—Ph) m.p. 181° C. 350 CH₃ NH(4-CONHCH₃—Ph) m.p. 196.3-198.1° C. 351 CH₃ NH(2-CONHC₂H₅—Ph) m.p. 166° C. 352 CH₃ NH(3-CONHC₂H₅—Ph) m.p. 155° C. 353 CH₃ NH(4-CONHC₂H₅—Ph) m.p. 190.8-193.4° C. 354 CH₃ NH(2-CONHC₃H₇-n-Ph) m.p. 165° C. 355 CH₃ NH(3-CONHC₃H₇-n-Ph) paste 356 CH₃ NH(4-CONHC₃H₇-n-Ph) m.p. 174.7-175.9° C. 357 CH₃ NH(2-CONHC₃H₇-i-Ph) m.p. 177° C. 358 CH₃ NH(3-CONHC₃H₇-i-Ph) m.p. 158° C. 359 CH₃ NH(4-CONHC₃H₇-i-Ph) m.p. 223.7-225.9° C. 360 CH₃ NH(3-CONHC₄H₉-n-Ph) paste 361 CH₃ NH(4-CONHC₄H₉-n-Ph) m.p. 157.4-159.3° C. 362 CH₃ NH(3-CONHC₄H₉-t-Ph) paste 363 CH₃ NH(4-CONHC₄H₉-t-Ph) m.p. 229.4-231.1° C. 364 CH₃ NH(2-CONHPh—Ph) m.p. 172-174° C. 365 CH₃ NH(4-CONHPh—Ph) m.p. 258.2-249.1° C. 366 CH₃ NH(2-CON(CH₃)₂—Ph) m.p. 153° C. 367 CH₃ NH(3-CON(CH₃)₂—Ph) m.p. 143° C. 368 CH₃ NH(4-CON(CH₃)₂—Ph) m.p. 176.8-178.6° C. 369 CH₃ NH(3-CON(C₂H₅)₂—Ph) paste 370 CH₃ NH(4-CON(C₂H₅)₂—Ph) m.p. 157.4-160.2° C. 371 CH₃ NH(3-CONHC₆H₁₃-n-Ph) paste 372 CH₃ NH(3-CONH(4-Cl—Ph)—Ph) paste 373 CH₃ NH(3-CO—Q₁₀—Ph) paste 374 CH₃ NH(2-COOH—Ph) m.p. 223° C. 375 CH₃ NH(3-COOH—Ph) m.p. 237° C. 376 CH₃ NH(2-C₃H₇-n-Ph) m.p. 76-78° C. 377 CH₃ NH(4-C₃H₇-n-Ph) m.p. 76-82° C. 378 CH₃ NH(2-C₃H₇-i-Ph) m.p. 116-118° C. 379 CH₃ NH(4-C₃H₇-i-Ph) m.p. 115-117° C. 380 CH₃ NH(4-C₄H₉-n-Ph) paste 381 CH₃ NH(4-C₄H₉-sec-Ph) m.p. 89-91° C. 382 CH₃ NH(2-C₄H₉-t-Ph) m.p. 114-115° C. 383 CH₃ NH(4-C₄H₉-t-Ph) paste 384 CH₃ NH(4-C₈H₁₇-n-Ph) m.p. 51-52° C. 385 CH₃ NH(2-Br—Ph) m.p. 139.8-142.1° C. 386 CH₃ NH(3-Br—Ph) m.p. 144.4-146.3° C. 387 CH₃ NH(4-Br—Ph) m.p. 122.9-124.4° C. 388 CH₃ NH(2,6-Cl₂—Ph) m.p. 168° C. 389 CH₃ NH(2,3-Cl₂—Ph) m.p. 151° C. 390 CH₃ NH(2-C₂H₅—Ph) m.p. 99.5-101.0° C. 391 CH₃ NH(3,5-(CH₃)₂—Ph) m.p. 135° C. 392 CH₃ NH(2,3-(CH₃)₂—Ph) m.p. 124° C. 393 CH₃ NH(3,4-(CH₃)₂—Ph) m.p. 116.8-118.2° C. 394 CH₃ NH(2,5-(CH₃)₂—Ph) m.p. 140° C. 395 CH₃ NH(2,4-(OCH₃)₂—Ph) m.p. 136° C. 396 CH₃ NH(2,5-(OCH₃)₂—Ph) m.p. 142° C. 397 CH₃ NH(3,4-(OCH₃)₂—Ph) m.p. 133° C. 398 CH₃ NH(3,5-(OCH₃)₂—Ph) m.p. 132° C. 399 CH₃ NH(4-OC₂H₅—Ph) m.p. 105.9-106.7° C. 400 CH₃ NH(2-NH₂—Ph) 401 CH₃ NH(3-NH₂—Ph) m.p. 168° C. 402 CH₃ NH(4-NH₂—Ph) m.p. 181° C. 403 CH₃ NH(4-CH₃CONH—Ph) m.p. 206° C. 404 CH₃ NH(4-PhCONH—Ph) m.p. 272° C. 405 CH₃ NH(4-(4-CH₃—Ph)SO₂NHPh) m.p. 179° C. 406 CH₃ NH(2-NHCOCH₃—Ph) 407 CH₃ NH(3-NHCOCH₃—Ph) 408 CH₃ NH(4-NHCOC₂H₅—Ph) 409 CH₃ NH(4-NHCOC₃H₇-i-Ph) 410 CH₃ NH(2-NHCOC₄H₉-t-Ph) 411 CH₃ NH(3-NHCOC₄H₉-t-Ph) 412 CH₃ NH(4-NHCOC₄H₉-t-Ph) 413 CH₃ NH(4-NHCOOCH₃—Ph) 414 CH₃ NH(2-NHCOOC₂H₅—Ph) 415 CH₃ NH(3-NHCOOC₂H₅—Ph) 416 CH₃ NH(4-NHCOOC₂H₅—Ph) 417 CH₃ NH(2-NHCOPh—Ph) 418 CH₃ NH(3-NHCOPh—Ph) 419 CH₃ NH(4-NHCO(6-Cl—Q₁)—Ph) 420 CH₃ NH(2-NHCO(4-CH₃—Q₈)—Ph) m.p. 189° C. 421 CH₃ NH(4-NHCO(4-CH₃—Q₈)—Ph) m.p. 260° C. 422 CH₃ NH(4-NHCONHC₂H₅—Ph) 423 CH₃ NH(2-NHSO₂CH₃—Ph) 424 CH₃ NH(3-NHSO₂CH₃—Ph) 425 CH₃ NH(4-NHSO₂CH₃—Ph) 426 CH₃ NH(2-NO₂—Ph) 427 CH₃ NH(3-NO₂—Ph) m.p. 140° C. 428 CH₃ NH(2-OH—Ph) 429 CH₃ NH(3-OH—Ph) 430 CH₃ NH(4-OH—Ph) 431 CH₃ NH(2-O—COCH₃—Ph) 432 CH₃ NH(3-O—COCH₃—Ph) 433 CH₃ NH(4-O—COCH₃—Ph) 434 CH₃ NH(2-O—COC₄H₉-t-Ph) 435 CH₃ NH(3-O—COC₄H₉-t-Ph) 436 CH₃ NH(4-O—COC₄H₉-t-Ph) 437 CH₃ NH(3-O—COPh—Ph) 438 CH₃ NH(4-O—COPh—Ph) 439 CH₃ NH(2-O—CO(4-CH₃—Q₈)—Ph m.p. 112° C. 440 CH₃ NH(3-O—CO(4-CH₃—Q₈)—Ph m.p. 152° C. 441 CH₃ NH(4-O—CO(4-CH₃—Q₈)—Ph m.p. 167° C. 442 CH₃ NH(2-O—COOC₂H₅—Ph) 443 CH₃ NH(3-O—COOC₂H₅—Ph) 444 CH₃ NH(4-O—COOC₂H₅—Ph) 445 CH₃ NH(4-O—COOC₂H₅—Ph) 446 CH₃ NH(4-CH₃SO₂—Ph) 447 CH₃ NH(4-CF₃SO₂—Ph) 448 CH₃ NH(5-CH₃—Q₁₈) m.p. 156° C. 449 CH₃ NH(2-CH₃—Q₁₉) m.p. 189° C. 450 CH₃ NH(4,6-(CH₃)₂—Q₁₁) paste 451 CH₃ NHCH₂CONH(4-Cl—Ph) m.p. 211° C. 452 CH₃ NHCH₂CONH(4-CH₃—Ph) m.p. 212° C. 453 CH₃ NHCH₂CONH(4-OCH₃—Ph) m.p. 188° C. 454 CH₃ NHCH₂CONHCH₂(4-CH₃—Ph) paste 455 CH₃ Q₂₀-(4-CO(4-CH₃—Q₈)) m.p. 234° C. 456 CH₃ NH-(5-Br—Q₁₁) 457 CH₃ NH-(4,6-(Cl)₂—Q₁₁) 458 CH₃ NH-(4,6-(CH₃)₂—Q₁₁) m.p. 153° C. 459 CH₃ NH—Q₁ 460 CH₃ NH—Q₂₁ 461 CH₃ NH-(4-CH₃—Q₂₁) 462 CH₃ NH-(4-Ph—Q₂₁) 463 CH₃ NH-(5-CF₃—Q₁₉) 464 CH₃ NH-(5-SC₂H₅—Q₁₉) 465 CH₃ NH-(3-Cl-5-CF₃—Q₂) 466 CH₃ NH-(4,6-(CH₃)₂—Q₂) 467 CH₃ NH—Q₂₂ 468 CH₃ NH(CH₂)₂NH—CO(4-CH₃—Q₈) 469 CH₃ NH(CH₂)₃NH—CO(4-CH₃—Q₈) 470 CH₃ NH(CH₂)₆NH—CO(4-CH₃—Q₈) 471 CH₃ NH(CH₂)₁₂NH—CO(4-CH₃—Q₈) 472 CH₃ NH(Ph)—NH₂ 473 CH₃ NHNHPh 474 CH₃ NHNHCOCH₃ 475 CH₃ NHNHCOC₆H₁₃-n 476 CH₃ NHNHCOC₁₂H₂₅-n 477 CH₃ NHNHCOCF₃ 478 CH₃ NHNHCO(4-Cl—Ph) 479 CH₃ NHNHCO(4-CH₃—Ph) 480 CH₃ NHNHCO(4-OCH₃—Ph) 481 CH₃ NHNHCOOCH₃ 482 CH₃ NHNHCOO—Ph 483 CH₃ NHNHCOO—CH₂Ph 484 CH₃ NHNHCONH₂ 485 CH₃ NHNHCONHCH₃ 486 CH₃ NHNHCONH—Ph 487 CH₃ NHNHSO₂CH₃ 488 CH₃ NHNHSO₂—Ph 489 CH₃ NHOC₂H₅ 490 CH₃ NHOC₃H₇-n 491 CH₃ NHOC₃H₇-i 492 CH₃ NHOC₄H₉-n 493 CH₃ NHOC₄H₉-t 494 CH₃ N(CH₃)OCH₃ 495 CH₃ NHOCH₂CH═CH₂ 496 CH₃ N(OH)(4-Cl—Ph) m.p. 186° C. (decomp.) 497 CH₃ N(OCH₃)(4-Cl—Ph) m.p. 98° C. 498 CONH₂ NH₂ m.p. 270° C. (sublim.) 499 CH₃ NH(3-Cl-4-CH₃—Ph) m.p. 114° C. Note: “cyclo” means a cyclic C₆H₁₁ group.

Table 2 shows ¹H-NMR data of the 1,2,3-thiadiazole derivatives having a physical property expressed by the word “oil”, “paste” or “NMR” in Table 1.

TABLE 2 No ¹H-NMR [CDCl₃/TMS, δ value (ppm) 24 0.879(5, 3H), 1.255(br, 8H), 1.75(m, 2H), 2.974(s, 1H), 4.340(t, 2H). 64 2.97(s, 6H), 4.68(s, 4H). 96 1.595(s, 1H), 1.757(s, 6H), 2.910(s, 3H), 5.98 (br, 1H). 97 1.305(d, 2H), 1.85(br, 1H), 2.903(s, 3H), 3.735(m, 2H), 4.25(m, 1H), 6.42(br, 1H). 102 1.00(t, 6H), 2.30(m, 1H), 2.950(s, 3H), 3.800 (s, 3H), 4.740(m, 1H), 6.42(br, 1H). 114 1.342(d, 6H), 2.948(s, 3H), 4.567(sept, 1H), 6.743(d, 1H), 7.011(d, 1H), 7.23-7.28(m, 2H), 7.659(s, 1H). 118 1.2695(d, 6H), 2.9355(sept, 1H), 2.9868(s, 3H), 7.1260(d, 1H), 7.32-7.40(m, 3H), 7.47(br, s, 1H). 140 2.818(s, 3H), 3.482(s, 3H), 7.11(m, 2H), 7.36 (m, 3H). 144 2.792(s, 3H), 3.25(m, 1H), 3.822(s, 3H), 5.05 (m, 1H), 6.32(br, 1H), 7.05-7.40(m, 5H). 150 1.26(t, 3H), 2.90(s, 3H), 3.74(q, 2H), 6.11 (d, 1H), 8.03(br, d, 1H). 151 2.637(t, 1H), 2.971(s, 1H), 4.425(m, 2H), 6.374(d, 1H), 7.13(br, d, 1H). 154 1.01(m, 3H), 1.39(q, 3H), 1.65(m, 2H), 2.94 (s, 3H), 3.10(m, 1H), 6.07(m, 1H), 7.05(br, t, 1H). 186 1.33(d, 6H), 4.13(m, 1H). 193 1.487(d, 6H), 3.73(sept, 1H), 4.365(d, 2H), 6.78(br, s, 1H) 213 1.345(d, 6H), 4.568(s, 1H), 6.70-7.30(m, 4H), 7.92(br, s, 1H). 227 1.20-1.40(m, 10H), 2.53(m, 1H), 2.89(m, 1H), 7.05-7.50(m, 4H), 8.30(br, s, 1H). 228 1.20-1.40(m, 10H), 2.50(m, 1H), 4.55(m, 1H), 6.72(q, 1H), 7.0-7.3(m, 3H), 8.30(br, s, 1H). 242 0.98(t, 3H), 1.49(m, 2H), 1.84(m, 2H), 4.50 (t, 2H), 4.63(d, 2H), 7.3-7.6(m, 5H), 10.23 (br, s, 1H). 246 0.98(t, 3H), 1.49(m, 2H), 1.84(m, 2H), 4.50 (t, 2H), 4.63(d, 2H), 7.3-7.6(m, 5H), 10.23 (br, s, 1H). 264 4.000(s, 3H), 5.854(s, 2H), 7.039(s, 1H), 7.142(s, 1H), 7.742(s, 1H). 265 4.001(s, 3H), 6.104(s, 2H), 7.934(s, 1H), 8.378(s, 1H). 267 7.3-7.5(m, 3H), 8.12(q, 2H) 273 7.1-7.5(m, 4H) 282 1.41(t, 3H), 2.27(s, 3H), 4.44(q, 2H), 5.88 (s, 2H), 7.2-7.6(m, 4H). 296 0.939(t, 3H), 1.45(m, 2H), 1.65(m, 2H), 2.970 (s, 3H), 3.82(m, 2H), 5.75(d, 1H), 6.48(d, 1H). 343 1.38(t, 3H), 2.96(s, 3H), 4.32(dd, 2H), 7.47 (t, 1H), 7.85(d, 1H), 8.00-8.05(br, 2H), 8.21 (br, 1H). 355 0.86(t, 3H), 1.46(m, 2H), 2.87(s, 3H), 3.07 (dd, 2H), 6.43(m, 1H), 7.39(d, 2H), 7.97(br, 1H), 8.10(m, 1H), 9.75(br, 1H). 360 0.92(t, 3H), 1.36(m, 2H), 1.51(m, 2H), 3.21 (dd, 2H), 6.21(br, 1H), 7.44(d, 2H), 7.98(s, 1H), 8.08(br, 1H), 9.19(br, 1H). 362 1.36(s, 9H), 2.84(s, 3H), 6.05(s, 1H), 7.34 (m, 2H), 7.81(s, 1H), 7.90(m, 1H), 9.41(br, 1H). 369 1.03-1.21(m, 6H), 3.19(dd, 2H), 3.41(dd, 2H), 6.87(d, 1H), 7.24(m, 2H), 7.73(d, 1H), 10.21 (br, 1H). 371 0.89(t, 3H), 1.20-1.70(m, 8H), 3.24(dd, 2H), 6.21(br, 1H), 7.40-7.50(m, 1H), 7.99(s, 1H), 8.05(br, 1H), 9.01(br, 1H). 372 2.95(s, 3H), 7.25-7.95(m, 7H), 8.06-8.14(br, 2H), 8.56(br, 1H). 373 2.89(s, 3H), 3.4-3.8(br, 8H), 7.02(d, 1H), 7.35(t, 1H), 7.47(br, 1H), 7.87(d, 1H), 9.53 (br, 1H). 380 0.93(t, 3H), 1.37(m, 2H), 1.59(m, 2H), 2.61 (t, 2H), 2.97(s, 1H), 7.22(d, 2H), 7.45(d, 2H), 7.53(br, 1H). 383 1.32(s, 9H), 2.96(s, 3H), 7.34(d, 2H), 7.49 (d, 2H), 7.88(br, 1H). 450 2.42(s, 6H), 2.90(s, 3H), 6.82(s, 1H), 8.6-9.5 (br, 1H). 454 2.28(s, 3H), 2.81(s, 3H), 3.92(d, 2H), 4.26 (d, 2H), 7.12(m, 4H), 8.51(br, 1H), 9.08(br, 1H).

The 1,2,3-thiadiazole derivatives of the general formula (I) or salts thereof according to the present invention are useful for agricultural and horticultural disease control. For example, the compounds listed in Table 1 are very effective in controlling various diseases, for instance, rice blast (Pyricularia oryzae), rice sheath blight (Rhizoctonia solani), rice helminthosporium leaf spot (Cochliobolus miyabeanus), powdery mildew of various host plants, such as powdery mildew of barley and wheat (Erysiphe graminis), oats crown rust (Puccinia coronata), rust of other plants, tomato late blight (Phytophthora infestans), late blight or Phytophthora rots of other plants, downy mildew of plants, such as cucumber downy mildew (Pseudoperonospora cubensis) and grape downy mildew (Plasmopara viticola), apple scab (Venturia inaequalis), apple alternaria leaf spot (Alternaria mali), pear black spot (Alternaria kikuchiana), citrus melanose (Diaporthe citri), cucumber bacterial blight (Pseudomonas syringae pv. lachrymans), tomato bacterial wilt (Pseudomonas solanacearum), cabbage black rot (Xanthomonas campestris), citrus canker (Xanthomonas citri (Hasse) Dowson), rice bacterial leaf blight (Xanthomonas oryzae), cabbage bacterial soft rot (Erwinia carotovora), and tobacco mosaic (Tobacco mosaic virus).

The agricultural and horticultural disease controller of the present invention is markedly effective in controlling the above-exemplified diseases which damage paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornamental plants, and the like. Therefore, the desired effects of the agricultural and horticultural disease controller of the present invention can be obtained by applying the disease controller to the paddy field water, stalks and leaves of fruit trees, vegetables, other crops, flowers and ornamental plants, soil, etc., at a season at which the diseases are expected to occur, before their occurrence or at the time when their occurrence is confirmed.

In general, the agricultural and horticultural disease controller of the present invention is used after being prepared into a conveniently usable form according to an ordinary manner for preparation of agrochemicals.

That is, the 1,2,3-thiadiazole derivative of the general formula (I) or salt thereof according to the present invention and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier used in the present invention may be either solid or liquid. As the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon, i.e. synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture thereof.

The liquid carrier is that which itself has solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oils; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as di-methylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not to be used at all.

To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

Adjuvants such as silicon oils may also be used as a defoaming agent.

The content of the active ingredient may be varied as required. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50% by weight.

The present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient is used to control various diseases in the following manner. That is, it is applied to a crop on which the diseases are expected to occur, or a site where the occurrence of the diseases is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the diseases. For example, to control the diseases of paddy rice, said disease controller can be used by a method such as submerged application to a regular paddy field, application to a rice nursery bed, dressing of seeds for direct sowing on flooded paddy field, or seed disinfection.

The applying dosage of the present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient is varied depending upon various factors such as a purpose, diseases to be controlled, a growth state of a plant, tendency of disease occurrence, weather, environmental conditions, a preparation form, an application method, an application site and application time. It may be properly chosen in the range of 0.1 g to 10 kg (in terms of the active ingredient) per 10 ares depending upon purposes.

The present inventive agricultural and horticultural disease controller containing the 1,2,3-thiadiazole derivative of the general formula (I) or a salt thereof as an active ingredient may be used in admixture with other agricultural and horticultural disease controllers in order to expand both spectrum of controllable diseases and the period of time when effective applications are possible or to reduce the dosage.

Typical examples and test examples of the present invention are described below but they should not be construed as limiting the scope of the invention.

In the examples, parts are all by weight.

EXAMPLE 1

Each compound listed in Table 1 50 parts Xylene 40 parts Mixture of polyoxyethylene 10 parts nonylphenyl ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

EXAMPLE 2

Each compound listed in Table 1  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the above ingredients.

EXAMPLE 3

Each compound listed in Table 1 5 parts Mixed powder of bentonite and clay 90 parts  Calcium lignin sulfonate 5 parts

Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

EXAMPLE 4

Each compound listed in Table 1 20 parts Mixture of kaolin and synthetic, 75 parts high-dispersion silicic acid Mixture of polyoxyethylene  5 parts nonylphenyl ether and calcium alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1

Controlling Effect on Rice Blast by Submerged Application

Rice plants at the 5 to 6 leaf stage cultivated in a 1/10000-are pot were subjected to submerged application of a chemical containing each compound listed in Table 1 as an active ingredient, in a dosage of 200 g/10 a in terms of the active ingredient. After standing in a greenhouse for 1 week, the plants were inoculated with a suspension of spores of blast fungus (Pyricularia oryzae) by spraying.

After the inoculation, the plants were allowed to stand in a moist chamber for 1 day and then a greenhouse for 6 days to cause the disease sufficiently. Then, lesions in each leaf were counted and then compared with those on the untreated plot, and the controlling degree was calculated, whereby the effect was judged according to the following criterion.

Effect Controlling degree (%) A 100-95  B 94-85 C 84-60 D 59-0 

As a result of the above test, the compounds listed in Table 1 were found to have a marked blast-controlling activity. Of these compounds, the following were rated C or higher: compound Nos. 1 to 42, 44 to 61, 62 to 89, 92 to 95, 97 to 100, 103 to 131, 133 to 136, 138 to 140, 142, 144 to 166, 168 to 192, 194 to 196, 198 to 200, 202 to 222, 224, 225, 227 to 233, 237, 240 253 to 255, 268, 269, 272, 273, 276, 278, 287 to 296, 342 to 346, 348, 351, 354 to 357, 361, 362, 366, 369, 372, 374 and 375. In particular, the following were rated A, namely, the following had an excellent blast-controlling activity: compound Nos. 1, 3, 5 to 19, 21, 24 to 26, 28, 29, 32, 33, 37 to 40, 52, 54, 55, 57 to 59, 64 to 68, 70 to 74, 77 to 80, 84, 92, 93, 99, 103, 104 to 121, 123 to 125, 128, 130, 131, 138, 145, 146, 149, 152, 153, 156, 157, 159, 160, 169, 172 to 174, 175 to 192, 194, 198, 199, 202, 208 to 210, 213, 215 to 221, 224, 225, 227 to 229, 233, 237, 253, 278, 288 to 290, 294, 343, 344, 346, 355, 356, 362, 372, 374 and 375.

Test Example 2

Controlling Effect on Barley Powdery Mildew

Barley plants at the 3.5 leaf stage cultivated in a pot were applied with a spray mix containing each compound listed in Table 1 as an active ingredient at the concentration of 200 ppm. After standing thus treated plants in a greenhouse for 1 week, the plants were inoculated with spores of powdery mildew fungus (Erysiphe graminis f. sp. hordei)

After the inoculation, the plants were allowed to stand in a greenhouse for 1 week to cause the disease sufficiently. Then, lesions in each leaf were counted and then compared with those on the untreated plot, and the controlling degree was calculated, whereby the effect was judged according to the following criterion.

Effect Controlling degree (%) A 100-80  B 79-60 C 59-0 

As a result of the above test, the compounds listed in Table 1 were found to have a marked powdery mildew-controlling activity. Of these compounds, the following were rated B or higher: compound Nos. 7 to 9, 15, 16, 33, 40, 66, 72, 84, 104 to 107, 111 to 113, 115 to 117, 122 to 124, 128, 130, 139, 145, 180, 193, 194, 215, 217, 218 and 224. In particular, the following were rated A: compound Nos. 7 to 9, 15, 16, 33, 40, 66, 72, 84, 104 to 107, 111 to 113, 115 to 117, 122 to 124, 128, 130, 139, 145, 180, 193, 215, 217, 218 and 224.

Referential Production Example 1 Production of sodium 4-ethyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 8)

To a solution of 0.13 g of sodium hydroxide in 3 ml of ethanol was added 0.5 g of 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid, and the reaction was carried out at room temperature for 24 hours.

After completion of the reaction, the solvent was distilled off under reduced pressure and the crude product thus obtained was recrystallized from ethanol to obtain 0.44 g of the desired-compound.

Physical property: m.p. 250° C. (decomp.).

Yield: 77%.

Referential Production Example 2 Production of t-butylammonium 4-ethyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 185)

In 3 ml of ethanol was dissolved 0.4 g of 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid, after which 0.19 g of t-butylamine was added to the solution and the reaction was carried out at room temperature for 24 hours.

After completion of the reaction, the crystals precipitated in the reaction solution were collected by filtration and washed with n-hexane to obtain 0.54 g of the desired compound.

Physical property: m.p. 105-107° C.

Yield: 93%.

Referential Production Example 3 Production of N-isopropyl-5-(N′-isopropyl-carbamoyl)-1,2,3-thiadiazol-4-ylacetamide (Compound No. 252)

In dimethyl sulfoxide was suspended 0.1 g of sodium hydride, after which 1 g of isopropylamine was added to the suspension, followed by ice-cooling. Then, 0.5 g of methyl 5-methoxycarbonyl-1,2,3-thiadiazol-4-ylacetate was added and the resulting mixture was stirred at room temperature and allowed to stand for 24 hours.

After completion of the reaction, the reaction mixture was poured into ice water and the desired compound was extracted with ethyl acetate. The extracted solution was washed with water, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified by a column chromatography to obtain 0.23 g of the desired compound.

Physical property: m.p. 146-156° C.

Yield: 37%.

Referential Production Example 4 Production of ethyl 4-(2-methylphenoxymethyl)-1,2,3-thiadiazole-5-carboxylate (Compound No. 281)

In 20 ml of dimethylformamide was suspended 0.5 g of sodium hydride, after which 1.57 g of 2-methylphenol was added to the suspension and the resulting mixture was stirred at room temperature for 5 minutes. The reaction mixture was cooled with ice, followed by adding thereto 3 g of ethyl 4-chloromethyl-1,2,3-thiadiazolecarboxylate, and the resulting mixture was stirred at room temperature and allowed to stand for 24 hours.

After completion of the reaction, the reaction mixture was poured into ice water and the desired compound was extracted three times with ethyl acetate. The extracted solution was washed with water, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 1.33 g of the desired compound was obtained.

Physical property: nD 1.5579 (20.1° C.).

Yield: 33%.

Referential Production Example 5 Production of isopropyl 4-methyl-1,2,3-thiadiazole-5-carboxylate (Compound No. 18)

To 1.0 g (6.9 mmoles) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid were added 40 ml of thionyl chloride and 2 drops of dimethylformamide at room temperature, and the resulting mixture was refluxed with heating or 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the excess thionyl chloride was distilled off and 7.0 ml of tetrahydrofuran was added to the residue. Then, 2.1 g (21 mmoles) of triethylamine and 0.83 g (13.8 mmoles) of isopropanol were added and the resulting mixture was stirred at room temperature for 18 hours, after which a saturated aqueous sodium chloride solution was added. The desired compound was extracted with ethyl acetate and the organic layer was washed successively with diluted hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (n-hexane:ethyl acetate=10:1) to obtain 1.0 g of the desired compound.

Physical property: nD 1.4400 (14.3° C.).

Yield: 79%. 

What is claimed is:
 1. A method for controlling agricultural and horticultural diseases of plants which comprises applying a 1,2,3 thiadiazole derivative represented by the general formula (I), or a salt thereof at an active amount to control said plant diseases:

wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)-alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} a group represented by the formula:

(wherein R³ and R⁴, which may be the same or different, are hydrogen atoms, (C₁-C₁₂)alkyl groups or halo(C₁-C₁₂)alkyl groups, m is zero or an integer of 1 to 6, and R⁵ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups), {circle around (12)} a group represented by the formula:

(wherein R³, R⁴ and m are as defined above, and R⁶ and R⁷, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups; (C₁-C₁₂)alkylthio (C₁-C₆)alkyl groups; cyano(C₁-C₁₂)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; unsubstituted phenyl(C₁-C₆)alkyl groups; or substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; R⁶ and R⁷ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula:

(wherein R³, R⁴, R⁶ and R⁷ are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula:

{{wherein R³, R⁴ and n are as defined above, A is

(wherein R⁹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group),

{wherein R⁹ is as defined above, and R¹⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group, R⁹ and R¹⁰ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R¹¹ (wherein R¹¹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group)}, or  —N(R¹⁰) (wherein R¹⁰ is as defined above), and R⁸ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group; a (C₁-C₁₂)alkylthio-(C₁-C₁₂)alkyl group; a cyano(C₁-C₁₂)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)-alkyl group; a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkyl-thio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkyl-thio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups}}, and R² is (i) a group represented by the formula: —X—R¹² wherein X is an oxygen atom or a sulfur atom, and R¹² is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₂₀)alkenyl group, {circle around (5)} a halo(C₂-C₂₀)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a hydroxy(C₁-C₆)alkyl group, {circle around (9)} a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group, {circle around (10)} a (C₁-C₁₂)alkylthio(C₁-C₁₂)alkyl group, {circle around (11)} a (C₃-C₆)cycloalkyl group, {circle around (12)} a (C₃-C₆)cycloalkyl(C₁-C₁₂)alkyl group, {circle around (13)} an unsubstituted phenyl group, a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkyl-thio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups, (C₂-C₆)alkynyl groups, and (C₁-C₆)alkoxy carbonyl(C₁-C₆)alkyloxy groups {circle around (15)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (16)} a substituted phenyl (C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (17)} a diphenyl(C₁-C₆)alkyl group, {circle around (18)} a phenoxy(C₁-C₆)alkyl group, {circle around (19)} a group represented by the formula: —B—N(R¹³)R¹⁴ {wherein B is a (C₁-C₆)alkylene group which may be substituted by a (C₁-C₆)alkyl group or a phenyl group, and R¹³ and R¹⁴, which may be the same or different, are hydrogen atoms; formyl groups; (C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups;(C₂-C₁₂)-alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl, groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent; R¹³ and R¹⁴ being able to be taken together to represent a (C₄-C₅)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or  N—R¹¹ (wherein R¹¹ is as defined above)), {circle around (20)} a group represented by the formula: —C(R¹⁵)═C(R¹⁶)—R¹⁷ (wherein R¹⁵ is a hydrogen atom or a (C₁-C₆)alkyl group, R¹⁶ is a hydrogen atom, a halogen atom or a (C₁-C₆)alkyl group, and R¹⁷ is a nitro group, a cyano group, a (C₁-C₆)alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted aminocarbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C₁-C₁₂)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, R¹⁵ and R¹⁷ being able to be taken together to represent a (C₃-C₄)alkylene group which may be substituted by one or more (C₁-C₆)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula:

(wherein two R¹⁸'s which may be the same or different, are hydrogen atoms, (C₁-C₆)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent, and l is zero or an integer of 1 to 12), {circle around (22)} a 5- or 6-membered heterocyclic alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C₁-C₁₂)alkyl groups having on the ring a halogen atom or (C₁-C₆)alkyl group as the substituent {circle around (25)} (C₁-C₆)alkylcarbonyl(C₁-C₆)alkyol groups or {circle around (26)} (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyl groups}}, (ii) a group represented by the formula: —O—N═C(R¹⁹)R²⁰ {{wherein R¹⁹ and R²⁰, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (3)} nitro groups, {circle around (4)} cyano groups, {circle around (5)} (C₁-C₁₂)alkyl groups, {circle around (6)} halo(C₁-C₁₂)alkyl groups, {circle around (7)} (C₃-C₆)cycloalkyl groups, {circle around (8)} (C₂-C₁₂)alkenyl groups, {circle around (9)} (C₂-C₁₂)alkynyl groups, {circle around (10)} (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl groups, {circle around (11)} (C₁-C₁₂)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio, groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (16)} groups represented by the formula; —SR⁵ (wherein R⁵ is as defined above), or {circle around (17)} groups represented by the formula: —N(R⁶)R⁷ (wherein R⁶ and R⁷ are as defined above), R¹⁹ and R²⁰ being able to be taken together to represent {circle around (18)} a (C₃-C₆)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom}}, (iii) a group represented by the formula: —N(R²¹)R²² {{wherein R²¹ and R²², which may be the same or different, are, {circle around (2)} (C₁-C₁₂)alkyl groups, {circle around (3)} unsubstituted halo(C₁-C₁₂)alkyl groups, {circle around (4)} substituted halo(C₁-C₁₂)alkyl groups having a hydroxyl group or a (C₁-C₆)alkoxy group as the substituent, {circle around (5)} (C₂-C₁₂)alkenyl groups, {circle around (6)} (C₂-C₁₂)alkynyl groups, {circle around (7)} (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups, {circle around (8)} (C₁-C₁₂)alkylthio-(C₁-C₆)alkyl groups, {circle around (9)} cyano(C₁-C₁₂)alkyl groups, {circle around (10)} substituted cyano(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C₁-C₆)alkyl groups, {circle around (12)} substituted carbamoyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (13)} hydroxy (C₁-C₆)alkyl groups, di(C₁-C₆)alkoxy(C₁-C₆)alkyl groups in which the (C₁-C₆)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkyl groups, {circle around (16)} substituted (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenyl group, phenyl(C₁-C₆)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, unsubstituted phenyl groups, {circle around (7)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C₁-C₆)alkyl groups, 6) (C₁-C₆)alkoxy groups, 7) halo(C₁-C₆)alkoxy groups, 8) (C₁-C₆)alkylthio groups, 9) halo(C₁-C₆)alkylthio groups, 10) (C₂-C₆)alkenyl groups, 11) (C₂-C₆)alkynyl groups, 12) (C₁-C₆)alkylcarbonyl groups, 13) carboxyl group, 14) (C₁-C₁₂)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula:

(wherein R²³ and R²⁴, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula: —SO₂—R²⁵ (wherein R²⁵ is a hydrogen atom, hydroxyl group, a (C₁-C₁₂)alkyl group, a halo(C₁-C₆)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, unsubstituted 1,2,3 thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C₁-C₆)alkyl group or (C₁-C₆)alkoxy group as the substituent), 19) groups represented by the formula:

(wherein R²⁵ is as defined above), 20) groups represented by the formula:

(wherein R²⁶ is a (C₁-C₆)alkyl group, a phenyl group or a phenyl(C₁-C₆)alkyl group), 21) groups represented by the formula: —NH—SO₂—R²⁵ (wherein R²⁵ is as defined above), 22) groups represented by the formula:

(wherein R²⁵ is as defined above), and 23) groups represented by the formula:

(wherein R²⁶ is as defined above), 24) amino group, 25) (C₁-C₆)alkylureid groups, and 26) hydroxy group, {circle around (20)} substituted phenyl(C₁-C₆)-alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (20)}-1 phenylaminocarbonyl(C₁-C₆)alkyl groups and {circle around (20)}-2 substituted phenylaminocarbonyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula: —(CH₂)pNHR¹⁸ (wherein R¹⁸ is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R²¹ and R²² being able to be taken together to represent {circle around (24)} a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group}}, (iv) a group represented by the formula: —N(R⁶)NHR²⁷ {{wherein R⁶ is as defined above, and R²⁷ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a (C₂-C₁₂)alkynyl group, {circle around (6)} a (C₁-C₁₂)alkoxy(C₁-C₆)alkyl group, {circle around (7)} a (C₁-C₁₂)alkylthio(C₁-C₆)alkyl group, {circle around (8)} a cyano(C₁-C₁₂)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (12)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (13)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (14)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (15)} a group represented by the formula:

(wherein R⁶ and R⁷ are as defined above), or {circle around (16)} a group represented by the formula: —SO₂—R⁶ (wherein R⁶ is as defined above)}}, (v) a group represented by the formula: —NHN(R⁶)R²⁷ {{wherein R⁶ and R²⁷ are as defined above, R⁶ and R²⁷ being able to be taken together to represent ═C(R²⁸)R²⁹ (wherein R²⁸ and R²⁹, which may be the same or different, are hydrogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkyl groups; (C₃-C₆)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R²⁸ and R²⁹ being able to be taken together to represent a (C₃-C₆)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R⁶ and R²⁷ being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom}}, or (vi) a group represented by the formula: —N(R⁶)—OR³⁰ (wherein R⁶ is as defined above, and R³⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group, a halo(C₁-C₁₂)alkyl group, a (C₃-C₆)cycloalkyl group, a (C₂-C₁₂)alkenyl group, a (C₂-C₁₂)alkynyl group, an unsubstituted phenyl(C₁-C₆)-alkyl group, or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups).
 2. The method of claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} a group represented by the formula:

(wherein R³ and R⁴, which may be the same or different, are hydrogen atoms, (C₁-C₁₂)alkyl groups or halo(C₁-C₁₂)alkyl groups, m is zero or an integer of 1 to 6, and R⁵ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups), {circle around (12)} a group represented by the formula:

(wherein R³, R⁴ and m are as defined above, and R⁶ and R⁷, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups; (C₁-C₁₂)alkylthio-(C₁-C₆)alkyl groups; cyano(C₁-C₁₂)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; unsubstituted phenyl(C₁-C₆)alkyl groups; or substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; R⁶ and R⁷ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula:

(wherein R³, R⁴, R⁶ and R⁷ are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula:

[wherein R³, R⁴ and n are as defined above, A is

(wherein R⁹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group), —S—, —SO—, —SO₂—,

 {wherein R⁹ is as defined above, and R¹⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group, R⁹ and R¹⁰ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R¹¹  (wherein R¹¹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group)}, or —N(R¹⁰)—  (wherein R¹⁰ is as defined above), and R⁸ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group; a (C₁-C₁₂)alkylthio-(C₁-C₁₂)alkyl group; a cyano(C₁-C₁₂)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups], and R² is (i) a group represented by the formula: —X—R¹²  [wherein X is an oxygen atom or a sulfur atom, and R¹² is {circle around (1)} a hydrogen atom, {circle around (2)} (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₂₀)alkenyl group, {circle around (5)} a halo(C₂-C₂₀)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a hydroxy(C₁-C₆)alkyl group, {circle around (9)} a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group, {circle around (10)} a (C₁-C₁₂)alkylthio(C₁-C₁₂)alkyl group, {circle around (11)} a (C₃-C₆)cycloalkyl group, {circle around (12)} a (C₃-C₆)cycloalkyl(C₁-C₁₂)alkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups, (C₂-C₆)alkynyl groups and (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (16)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (17)} a diphenyl(C₁-C₆)alkyl group, {circle around (18)} a phenoxy(C₁-C₆)alkyl group, {circle around (19)} a group represented by the formula: —B—N(R¹³)R¹⁴  {wherein B is a (C₁-C₆)alkylene group which may be substituted by a (C₁-C₆)alkyl group or a phenyl group, and R¹³ and R¹⁴, which may be the same or different, are hydrogen atoms; formyl groups; (C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent; R¹³ and R¹⁴ being able to be taken together to represent a (C₄-C₅)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or N—R¹¹  (wherein R¹¹ is as defined above)}, {circle around (20)} a group represented by the formula: —C(R¹⁵)═C(R¹⁶)—R¹⁷  (wherein R¹⁵ is a hydrogen atom or a (C₁-C₆)alkyl group, R¹⁶ is a hydrogen atom, a halogen atom or a (C₁-C₆)alkyl group, and R¹⁷ is a nitro group, a cyano group, a (C₁-C₆)alkylcarbonyl group, a (C₁-C₆)alkoxycarbonyl group, a phenylcarbonyl group, or a substituted aminocarbonyl group having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, (C₁-C₁₂)alkyl groups, unsubstituted phenyl group, and substituted phenyl groups having one or more substituents which maybe the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, R¹⁵ and R¹⁷ being able to be taken together to represent a (C₃-C₆)alkylene group which may be substituted by one or more (C₁-C₆)alkyl group and/or an oxo group), {circle around (21)} a group represented by the formula:

 (wherein two R¹⁸'s, which may be the same or different, are hydrogen atoms, (C₁-C₆)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent, and l is zero or an integer of 1 to 12), or {circle around (22)} a 5- or 6-membered heterocyclic alkyl group having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (23)} a tri(C₁-C₆)alkylsilyl(C₁-C₆)alkyl groups, or {circle around (24)} 1,2,3-thiadiazol-5-yl-carbonyloxy-(C₁-C₁₂)alkyl groups having on the ring a halogen atom or (C₁-C₆)alkyl group as the substituent].
 3. The method for controlling agricultural and horticultural diseases of plants according to claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₆)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (11)} a group represented by the formula:

(wherein R³ and R⁴, which may be the same or different, are hydrogen atoms, (C₁-C₁₂)alkyl groups or halo(C₁-C₁₂)alkyl groups, m is zero or an integer of 1 to 6, and R⁵ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)alkyl group; or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups), {circle around (12)} a group represented by the formula:

(wherein R³, R⁴ and m are as defined above, and R⁶ and R⁷, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups; (C₁-C₁₂)alkylthio-(C₁-C₆)alkyl groups; cyano(C₁-C₁₂)alkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂C₆)alkynyl groups; unsubstituted phenyl(C₁-C₆)alkyl groups; or substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; R⁶ and R⁷ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain), {circle around (13)} a group represented by the formula:

(wherein R³, R⁴, R⁶ and R⁷ are as defined above, and n is an integer of 1 to 6), or {circle around (14)} a group represented by the formula:

{{wherein R³, R⁴ and n are as defined above, A is

(wherein R⁹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group),

{{wherein R⁹ is as defined above, and R¹⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group, R⁹ and R¹⁰ being able to be taken together to represent a (C₄-C₆)alkylene group which may contain, between adjacent carbon atoms of the carbon chain, an oxygen atom, a sulfur atom or  N—R¹¹ (wherein R¹¹ is a hydrogen atom, a (C₁-C₁₂)alkyl group or a halo(C₁-C₁₂)alkyl group), or —N(R¹⁰) (wherein R¹⁰ is as defined above), and R⁸ is a hydrogen atom; a (C₁-C₁₂)alkyl group; a halo(C₁-C₁₂)alkyl group; a (C₂-C₁₂)alkenyl group; a (C₂-C₁₂)alkynyl group; a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group; a (C₁-C₁₂)alkylthio-(C₁-C₁₂)alkyl group; a cyano(C₁-C₁₂)alkyl group; an unsubstituted phenyl group; a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted phenyl(C₁-C₆)-alkyl group; a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkyl-thio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups; an unsubstituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; or a substituted 5- or 6-membered heterocyclic ring having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆) alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkyl-thio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups}}, and R² is (iii) a group represented by the formula: —N(R²¹)R²² {{wherein R²¹ and R²², which may be the same or different, are {circle around (2)} (C₁-C₁₂)alkyl groups, {circle around (3)} unsubstituted halo(C₁-C₁₂)alkyl groups, {circle around (4)} substituted halo(C₁-C₁₂)alkyl groups having a hydroxyl group or a (C₁-C₆)alkoxy group as the substituent, {circle around (5)} (C₂-C₁₂)alkenyl groups, {circle around (6)} (C₂-C₁₂)alkynyl groups, {circle around (7)} (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups, {circle around (8)} (C₁-C₁₂)alkylthio (C₁-C₆)alkyl groups, {circle around (9)} cyano(C₁-C₁₂)alkyl groups, {circle around (10)} substituted cyano(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (11)} unsubstituted carbamoyl(C₁-C₆)alkyl groups, {circle around (12)} substituted carbamoyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenoxy group, phenylthio group and pyrazol-14-yl group, {circle around (13)} hydroxy (C₁-C₆)alkyl groups, {circle around (14)} di(C₁-C₆)alkoxy(C₁-C₆)alkyl groups in which the (C₁-C₆)alkoxy groups may be the same or different, {circle around (15)} unsubstituted (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyl groups, {circle around (16)} substituted (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyl groups having on the alkyl chain a substituent selected from the group consisting of (C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, (C₂-C₆)alkenyloxy groups, (C₂-C₆)alkynyloxy groups, (C₁-C₆)alkylthio groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkoxy groups, (C₁-C₆)alkoxycarbonyl(C₁-C₆)alkylthio groups, phenyl group, phenyl(C₁-C₆)alkyl group, phenoxy group, phenylthio group and pyrazol-1-yl group, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C₁-C₆)alkyl groups, 6) (C₁-C₆)alkoxy groups, 7) halo(C₁-C₆)alkoxy groups, 8) (C₁-C₆)alkylthio groups, 9) halo(C₁-C₆)alkyl-thio groups, 10) (C₂-C₆)alkenyl groups, 11) (C₂-C₆)alkynyl groups, 12) (C₁-C₆)alkylcarbonyl groups, 13) carboxyl group, 14) (C₁-C₁₂)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula:

(wherein R²³ and R²⁴, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula: —SO₂—R²⁵ (wherein R²⁵ is a hydrogen atom, hydroxyl group, a (C₁-C₁₂)alkyl group, a halo(C₁-C₆)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, unsubstituted 1,2,3 thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C₁-C₆)alkyl group or (C₁-C₆)alkoxy group as the substituent), 19) groups represented by the formula:

(wherein R²⁵ is as defined above), 20) groups represented by the formula:

(wherein R²⁶ is a (C₁-C₆)alkyl group, a phenyl group or a phenyl(C₁-C₆)alkyl group, 21) groups represented by the formula: —NB—SO₂—R²⁵ (wherein R²⁵ is as defined above), 22) groups represented by the formula:

(wherein R²⁵ is as defined above), and 23) groups represented by the formula:

(wherein R²⁶ is as defined above), {circle around (20)} substituted phenyl(C₁-C₆)alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula: —(CH₂)pNHR¹⁸ (wherein R¹⁸ is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R²¹ and R²² being able to be taken together to represent {circle around (24)} a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or {circle around (25)} a diaminomethylene group}}.
 4. The method of claim 2, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (i) a group represented by the formula: —X—R¹² [wherein X is an oxygen atom or a sulfur atom, and R¹² is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₂₀)alkenyl group, {circle around (5)} a halo(C₂-C₂₀)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a hydroxy(C₁-C₆)alkyl group, {circle around (9)} a (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl group, {circle around (11)} a (C₃-C₆)cycloalkyl group, {circle around (13)} an unsubstituted phenyl group, {circle around (14)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, and (C₁-C₆)alkoxycarbonyl-(C₁-C₆)alkyloxy groups, {circle around (15)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (16)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, and halo(C₁-C₆)alkoxy groups, {circle around (17)} a diphenyl(C₁-C₆)alkyl group, {circle around (18)} a phenoxy(C₁-C₆)alkyl group, {circle around (19)} a group represented by the formula: —B—N(R¹³)R¹⁴ {wherein B is a (C₁-C₆)alkylene group which may be substituted by a (C₁-C₆)alkyl group or a phenyl group, and R¹³ and R¹⁴, which may be the same or different, are hydrogen atoms; formyl groups; (C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; (C₁-C₁₂)alkylcarbonyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of hydrogen atom, halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, and halo(C₁-C₆)alkoxy groups; phenylcarbonyl groups; unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups; or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent; {circle around (21)} a group represented by the formula:

(wherein two R¹⁸'s, which may be the same or different, are hydrogen atoms, (C₁-C₆)alkylcarbonyl groups, phenylcarbonyl groups, unsubstituted 1,2,3-thiadiazol-5-yl-carbonyl groups, or substituted 1,2,3-thiadiazol-5-yl-carbonyl groups having a halogen atom or a (C₁-C₆)alkyl group as the substituent, and l is zero or an integer of 1 to 12), or (1,2,3-thiadiazol-5-yl-carbonyloxy(C₁-C₆)alkyl groups having on the ring a halogen atom or (C₁-C₆)alkyl group as the substituent].
 5. The method of claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (ii) a group represented by the formula: —O—N═C(R¹⁹)R²⁰ [wherein R¹⁹ and R²⁰, which may be the same or different, are {circle around (1)} hydrogen atoms, {circle around (2)} halogen atoms, {circle around (4)} cyano groups, {circle around (5)} (C₁-C₁₂)alkyl groups, {circle around (6)} halo(C₁-C₁₂)alkyl groups, {circle around (7)} (C₃-C₆)cycloalkyl groups, {circle around (8)} (C₂-C₁₂)alkenyl groups, {circle around (9)} (C₂-C₁₂)alkynyl groups, {circle around (10)} (C₁-C₁₂)alkoxy(C₁-C₁₂)alkyl groups, {circle around (11)} (C₁-C₁₂)alkoxycarbonyl groups, {circle around (12)} unsubstituted phenyl groups, {circle around (13)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (14)} unsubstituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, {circle around (15)} substituted 5- or 6-membered heterocyclic rings having one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, said substituted heterocyclic ring having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, {circle around (16)} groups represented by the formula; —SR⁵ (wherein R⁵ is as defined above), or {circle around (17)} groups represented by the formula: —N(R⁶)R⁷ (wherein R⁶ and R⁷ are as defined above), R¹⁹ and R²⁰ being able to be taken together to represent {circle around (18)} a (C₃-C₆)cycloalkane ring or {circle around (19)} a 5- or 6-membered heterocyclic ring containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom].
 6. The method of controlling agricultural and horticultural diseases of plants according to claim 4, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₁-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (iii) a group represented by the formula: —N(R²¹)R²² {{wherein R²¹ and R²², which may be the same or different, are {circle around (2)} (C₁-C₁₂)alkyl groups, {circle around (3)} unsubstituted halo(C₁-C₁₂)alkyl groups, {circle around (5)} (C₂-C₁₂)alkenyl groups, {circle around (6)} (C₂-C₁₂)alkynyl groups, {circle around (7)} (C₁-C₁₂)alkoxy(C₁-C₆)alkyl groups, {circle around (8)} (C₁-C₁₂)alkylthio-(C₁-C₆)alkyl groups, {circle around (9)} cyano(C₁-C₁₂)alkyl groups, {circle around (11)} unsubstituted carbamoyl(C₁-C₆)alkyl groups, {circle around (13)} hydroxy (C₁-C₆)alkyl groups, {circle around (15)} unsubstituted (C₁-C₆)alkoxy-carbonyl(C₁-C₆)alkyl groups, {circle around (17)} unsubstituted phenyl groups, {circle around (18)} substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of 2) nitro group, 3) cyano group, 5) halo(C₁-C₆)alkyl groups, 6) (C₁-C₆)alkoxy groups, 7) halo(C₁-C₆)alkoxy groups, 8) (C₁-C₆)alkylthio groups, 12) (C₁-C₆)alkylcarbonyl groups, 13) carboxyl group, 14) (C₁-C₁₂)alkoxycarbonyl groups, 15) methylenedioxy group, 16) phenyl group, 17) groups represented by the formula:

(wherein R²³ and R²⁴, which may be the same or different, are hydrogen atoms; (C₁-C₁₂)alkyl groups; halo(C₁-C₁₂)alkyl groups; (C₂-C₁₂)alkenyl groups; (C₂-C₁₂)alkynyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom), 18) groups represented by the formula: —SO₂—R²⁵ (wherein R²⁵ is a hydrogen atom, hydroxyl group, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, an unsubstituted phenyl group, a substituted phenyl group having as the substituent(s) one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups, unsubstituted 1,2,3thiadiazol-5-yl group, or substituted 1,2,3-thiadiazol-5-yl groups having halogen atom, (C₁-C₆)alkyl group or (C₁-C₆)alkoxy group as the substituent), 19) groups represented, by the formula:

(wherein R²⁵ is as defined above), 20) groups represented by the formula:

(wherein R²⁶ is a (C₁-C₆)alkyl group, a phenyl group or a phenyl(C₁-C₆)alkyl group), 21) groups represented by the formula: —NH—SO₂—R²⁵ (wherein R²⁵ is as defined above), 22) groups represented by the formula:

(wherein R²⁵ is as defined above), and 23) groups represented by the formula:

(wherein R²⁶ is as defined above), {circle around (20)} substituted phenyl(C₁-C₆)-alkyl groups having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, and halo(C₁-C₆)alkoxy groups, {circle around (21)} naphthyl groups, {circle around (22)} groups represented by the formula: —(CH₂)pNHR¹⁸ (wherein R¹⁸ is as defined above, and p is an integer of 1 to 12), or {circle around (23)} 5- or 6-membered heterocyclic rings having one or more atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, R²¹ and R²² being able to be taken together to represent {circle around (24)} a (C₄-C₆)alkylene group which may contain an oxygen atom between adjacent carbon atoms of the carbon chain, or a diaminomethylene group}}.
 7. The method of claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (iv) a group represented by the formula: —N(R⁶)NHR²⁷ [wherein R⁶ is as defined above, and R²⁷ is {circle around (1)} a hydrogen atom, {circle around (1)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a (C₂-C₁₂)alkynyl group, {circle around (8)} a cyano(C₁-C₁₂)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, and halo(C₁-C₆)alkoxy groups, {circle around (11)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (12)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups and halo(C₁-C₆)alkoxy groups, {circle around (13)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (14)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (15)} a group represented by the formula:

(wherein R⁶ and R⁷ are as defined above), or {circle around (16)} a group represented by the formula: —SO₂—R⁶ (wherein R⁶ is as defined above)].
 8. The method of claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (v) a group represented by the formula: —NHN(R⁶)R²⁷ [wherein R⁶ is as defined above and R²⁷ is {circle around (1)} a hydrogen atom, {circle around (1)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a (C₂-C₁₂)alkynyl group, {circle around (8)} a cyano(C₁-C₁₂)alkyl group, {circle around (9)} an unsubstituted phenyl group, {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, and halo(C₁-C₆)alkoxy groups, {circle around (11)} an unsubstituted phenyl(C₁-C₆)alkyl group, {circle around (12)} a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups and halo(C₁-C₆)alkoxy groups, {circle around (13)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (14)} a group represented by the formula:

(wherein R⁶ is as defined above), {circle around (15)} a group represented by the formula:

(wherein R⁶ and R⁷ are as defined above), or {circle around (16)} a group represented by the formula: —SO₂—R⁶ (wherein R⁶ is as defined above)], R⁶ and R²⁷ being able to be taken together to represent ═C(R²⁸)R²⁹ (wherein R²⁸ and R²⁹, which may be the same or different, are hydrogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkyl groups; (C₃-C₆)cycloalkyl groups; unsubstituted phenyl groups; substituted phenyl groups having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, (C₁-C₆)alkyl groups and (C₁-C₆)alkoxy groups; or 5- or 6-membered heterocyclic rings containing, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom; R²⁸ and R²⁹ being able to be taken together to represent a (C₃-C₆)cycloalkane ring or a 5- or 6-membered heterocyclic ring containing one or more sulfur atoms between adjacent carbon atoms of the carbon chain), or R⁶ and R²⁷ being able to be taken together with the nitrogen atom to which they are bonded, to represent a 5- or 6-membered heterocyclic ring which may contain, between adjacent carbon atoms of the carbon chain, one or more hetero atoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom].
 9. The method of claim 1, wherein R¹ is {circle around (1)} a hydrogen atom, {circle around (2)} a (C₁-C₁₂)alkyl group, {circle around (3)} a halo(C₁-C₁₂)alkyl group, {circle around (4)} a (C₂-C₁₂)alkenyl group, {circle around (5)} a halo(C₂-C₁₂)alkenyl group, {circle around (6)} a (C₂-C₁₂)alkynyl group, {circle around (7)} a halo(C₂-C₁₂)alkynyl group, {circle around (8)} a (C₃-C₆)cycloalkyl group, {circle around (9)} an unsubstituted phenyl group, or {circle around (10)} a substituted phenyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups, and R² is (vi) a group represented by the formula: —N(R⁶)—OR³⁰ (wherein R⁶ is as defined above, and R³⁰ is a hydrogen atom, a (C₁-C₁₂)alkyl group, a halo(C₁-C₁₂)alkyl group, a (C₃-C₆)cycloalkyl group, a (C₂-C₁₂)alkenyl group, a (C₂-C₁₂)alkynyl group, an unsubstituted phenyl(C₁-C₆)alkyl group, or a substituted phenyl(C₁-C₆)alkyl group having on the ring one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₂-C₆)alkenyl groups and (C₂-C₆)alkynyl groups).
 10. The method of claim 1, wherein the 1,2,3-thiadiazole derivative or salt 